Triclabendazole

Triclabendazole, sold under the brand name Egaten among others, is a medication used to treat fascioliasis and paragonimiasis.[1] It is very effective for both conditions.[1] Treatment in hospital may be required.[1] It is taken by mouth with typically one or two doses being required.[1]

Triclabendazole
Clinical data
Trade namesFasinex, Egaten, others
AHFS/Drugs.comMonograph
MedlinePlusa619048
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismOxidation to sulfone and sulfoxide metabolites
Elimination half-life22–24 hours
ExcretionFeces (>95%), urine (2%), milk (<1%)
Identifiers
IUPAC name
  • 5-Chloro-6-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.127.414
Chemical and physical data
FormulaC14H9Cl3N2OS
Molar mass359.658 g·mol−1
3D model (JSmol)
Melting point175 to 176 °C (347 to 349 °F)
SMILES
  • CSc3nc2cc(Cl)c(Oc1cccc(Cl)c1Cl)cc2[nH]3
InChI
  • InChI=1S/C14H9Cl3N2OS/c1-21-14-18-9-5-8(16)12(6-10(9)19-14)20-11-4-2-3-7(15)13(11)17/h2-6H,1H3,(H,18,19) Y
  • Key:NQPDXQQQCQDHHW-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Side effects are generally few, but can include abdominal pain and headaches.[1] Biliary colic may occur due to dying worms.[2] While no harm has been found with use during pregnancy, triclabendazole has not been studied well in this population.[2] It is a member of the benzimidazole family of medications for worms.[1]

Triclabendazole was approved for medical use in the United States in 2019.[3] It is on the World Health Organization's List of Essential Medicines.[4] For human use, it can be obtained from the World Health Organization.[2] It is also used in animals.[5]

Chemistry

It is a member of the benzimidazole family of anthelmintics. The benzimidazole drugs share a common molecular structure, triclabendazole being the exception in having a chlorinated benzene ring but no carbamate group. Benzimidazoles such as triclabendazole are generally accepted to bind to beta-tubulin therefore preventing the polymerization of microtubules.

History

Since late 1990s, triclabendazole became available as a generic drug, as patents expired in many countries. Many products were developed then. Among them, Trivantel 15, a 15% triclabendazole suspension, was launched by Agrovet Market Animal Health in the early 2000s. In 2009, the first triclabendazole injectable solution (combined with ivermectin) was developed and launched, also by Agrovet Market Animal Health. The product, Fasiject Plus, a triclabendazole 36% and ivermectin 0.6% solution, is designed to treat infections by Fasciola hepatica (both immature and adult liver flukes), roundworms and ectoparasites, as well.

Fasinex is a brandname for veterinary use while Egaten is a brandname for human use.

References
  1. World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. pp. 94, 96. hdl:10665/44053. ISBN 9789241547659.
  2. Wolfe, M. Michael; Lowe, Robert C. (2014). "Benzimidazoles". Pocket Guide to GastrointestinaI Drugs. John Wiley & Sons. p. PT173. ISBN 9781118481554. Archived from the original on 20 December 2016.
  3. "Egaten (triclabendazole)" (PDF). FDA. Retrieved 18 February 2019.
  4. World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  5. "Triclabendazole - Drugs.com". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 10 December 2016.

Further reading
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